Sylvester James, Jr. (September 6, 1947 – December 16, 1988), better known as Sylvester, was an American disco and soul singer-songwriter. Known for his flamboyant and androgynous appearance, he was often described as a drag queen, although he repeatedly rejected such a description. Responsible for a string of hit singles in the late 1970s, Sylvester became known in the United States under the moniker of the "Queen of Disco."

On September 20, 2004, Sylvester's anthem record, "You Make Me Feel (Mighty Real)," was inducted into the Dance Music Hall of Fame. A year later, on September 19, 2005, Sylvester himself was inducted into the Dance Music Hall of Fame for his achievement as an artist. His life has been recorded in a biography and made the subject of a documentary and a musical.

Sylvester James was born on September 6, 1947 in the Watts district of Los Angeles, California.[1] His mother, Letha Weaver, had been raised outside of the Arkansas town of Palestine into a black American family who were relatively well-off, being farmers who owned their own land.[2] Letha's own biological mother, Gertha Weaver, was unmarried and too sickly to care for her child, and so Gertha's sister Julia, known to the family as JuJu, took on the role of Letha's adoptive mother.[1] In the late 1930s, Julia and her husband, Egypt Morgan, took part in the Great Migration of African-Americans out of the Southern United States, thereby moving from Arkansas to Watts.[1] It was here that Letha was largely raised and where she met and married her first husband, Sylvester "Sweet" James, with the couple moving into a small cottage owned by Letha's parents. Their first child, whom they named Sylvester after his father, was soon to be followed by the birth of John Wesley in 1948 and Larry in 1950.[1] In keeping with the cultural customs of their environment, Sylvester and his brothers became better known in their predominantly African-American community by their nicknames, with Sylvester's being "Dooni."[3] Sylvester's father was an adulterer and left his wife and children when they were still young; his son later lambasted him as a "lowlife."[4] Letha and her three sons moved to a downtown housing project named Aliso Village before moving back into her parental home at 114th Street in Watts.[5]

Like most of her family, Letha was a devout adherent of the Pentecostal denomination of Christianity, regularly attending the Palm Lane Church of God in Christ in South Los Angeles. Sylvester and his brothers were made to regularly attend this church, and he developed a particular interest in the gospel music that was performed there.[6][7] Having been an avid singer since the age of three, Sylvester regularly joined in with gospel performances, and he sang the song "My Buddy" at the funeral of one of the other children in the Park Lane congregation.[8] The young Sylvester was often accused of effeminacy, and recognized his own homosexuality from an early age. At age eight, he engaged in sexual activity with a far older man at the church—at the time rumored to be the church organist—although he would always maintain that this was consensual, and not an example of sexual molestation.[9] Taken to a doctor after receiving injuries during anal sex with this man, the doctor first informed Letha that her son was gay, something that she could not accept, viewing homosexual activity as a perversion and a sin.[6] News of Sylvester's homosexual activity soon spread through the church congregation, and feeling unwelcome, he ceased his attendance aged 13.[7][9][10]

During Sylvester's childhood, his mother gave birth to three more children by different fathers before marrying a neighbor named Robert "Sonny" Hurd in the early 1960s. They adopted three foster children. A supervisor at aerospace manufacturer North American Rockwell, Hurd's job increased the family income, and they were able to move into a more expensive, predominantly white neighborhood on 97th Street north of Watts. Hurd later bought much local real estate.[11] The family were able to live more extravagantly on their increasing income, although the relationship between Sylvester and both his mother and stepfather was strained. Eventually, in the midst of a heated argument with his mother, she proclaimed that if he didn't like the changes that were going on in the house then he could leave, which he did.[12]

Now homeless, Sylvester spent much of the next decade staying with friends and relatives, in particular his grandmother Julia, who expressed no disapproval of his homosexuality, having been a friend of a number of gay men in the 1930s. On occasion, he returned to his mother and step-father's house for a few days at a time, particularly to spend time with his younger sisters, Bernadette and Bernadine.[13] Aged 15, he began frequenting local gay clubs and built up a group of friends from the local gay black community, eventually forming themselves into a gang which they called the Disquotays.[9][14] Alongside Sylvester—still using the nickname of "Dooni"—the other members of the Disquotays included a number of other local gays: Tiki, Monique, Diane, Shelley Newman, Jay Freeman, Barbara, Garetha, Tammi, Shirley Floyd, Jackie Kennedy, Jackie Hoyle, Cleola Balls, Miss LaLa, Miss Louella, Miss Marcia, Larry Hines, and the only white member, Benedetta Barzini.[15][16] His best friend among the Disquotays was a trans woman named Duchess, who earned her money as a prostitute, a job that Sylvester refused to engage in.[17] The group held lavish house parties, sometimes at the home of their friend, R&B singer Etta James, in which they dressed up in female clothing and wigs, constantly trying to outdo one another in appearance, devoting themselves to "the look, the entrance, and the scene".[18]

"Dooni [Sylvester] and the Disquotays wandered the streets of South Central in the 1960s done up like women, and threw ferocious gay parties in neighborhoods whose strongest institutions were conservative black churches. It's tempting to see them as fearless and heroic, defiant sissies who were forerunners of Stonewall and sixties counterculture, part of the dawning of gay liberation and African-American civil rights organizing."

His boyfriend during the latter part of the 1960s was a young man named Lonnie Prince; well-built and attractive, many of Sylvester's friends described the pair as being "the It couple," akin to "the hot couple on campus at high school."[20] Sylvester often hitchhiked around town while in female dress; such activity carried a risk of arrest and prosecution, for transvestism was illegal in California at the time.[20] Although avoiding imprisonment for this crime, he would however be arrested for shoplifting on several occasions.[14] He found work in a variety of different professions in order to earn money, including cooking in McDonalds—where he was fired for refusing to wear a hairnet—collecting money at the parking garage of an airport, working in a hair salon, at a department store, and as a make-up artist at a mortuary, preparing the corpses for their funerals.[21] In the 1960s the African-American Civil Rights Movement was at its peak, but Sylvester and his friends did not take an active role within it. During the Watts Riots between members of the black community and the predominantly white police force, they joined in with the widespread rioting and looting, but rather than taking food and technical goods, they stole such items as "wigs, hairspray and lipstick."[19]

Meanwhile, he had been enrolled at Jordan High School, and although he rarely attended and took little interest in formal education, he graduated in 1969 at the age of 21. In his graduation photograph, he appeared in drag wearing a blue chiffon prom dress and beehive hairstyle.[14] By the end of the decade, the Disquotays had begun to drift apart, with a number of them abandoning cross-dressing as a hobby, and others recognizing that they were trans women and deciding to undergo sex reassignment surgery. Whereas his best friend, Duchess, considered herself female and decided to go for the surgery, Sylvester always considered himself male and enjoyed using his penis as the penetrative partner in anal sex. He began to tone down the feminine nature of his clothing, aiming for a more androgynous look which combined male and female items of clothing and which was influenced by the fashions of the hippie movement.[22]

While still in Los Angeles, Sylvester met a fellow gay black man named Reggie Dunnigan at the Whisky a Go Go bar. Impressed by Sylvester's androgynous outfit and flamboyant personality, Dunnigan encouraged his new friend to move to the city of San Francisco in Northern California, where he could join him as one of the "Chocolate Cockettes"—black members of an avant-gardeperformance art drag troupe known as The Cockettes.[23] The Cockettes had been founded on New Year's Day 1970 by a white drag queen going by the name of Hibiscus (1949–1982). They had begun holding performances at the Palace Theater in North Beach where they parodied popular culture, gaining a local cult following. Involved in the Gay Liberation movement that had been sparked by the Stonewall riots in 1969, they were influenced by the ethos of the hippie movement, living communally, embracing free love, and consuming large quantities of illicit substances like marijuana and LSD.[24] With the Disquotays disbanded, Sylvester had become tired of life in Los Angeles, and was attracted by San Francisco's reputation as a haven for gay and counter-cultural individuals. He made his way to the city, where he stayed in the Cockettes' communal home for a few days. They were very impressed with his falsetto singing voice and his ability to play the piano, and asked him to appear in an upcoming show, Radio Rodeo.[25] Sylvester agreed, and one of his first performances involved singing the theme song of The Mickey Mouse Club while dressed in a cowgirl skirt.[26]

"Sylvester shared the Cockettes' affinity for outrageous flaming, their celebration of sex and gayness, their love of acid and good hash, and their bent movie-musical fantasies. Like them, he was making himself up, fantasizing a self into existence. But he usually stood a few feet back, among the Cockettes but never quite one of them. His drag and makeup, for one thing, were almost staid in comparison with the Cockettes'; they preferred facial designs that were almost like war paint, and clothing that didn't make sense. Sylvester wore simple period dresses onstage, and created the face of a sane, pretty woman."

Moving into the Cockettes' communal residence, the middle flat in a 19th-century house which they had named the Haight Street Chateau, Sylvester had to share a room with two other members, demarcating off his sleeping space with floral curtains. He found the flat too crowded, and had difficulty with the lack of privacy. After a year, he moved into a new house on Market Street with Cockettes John Rothermel and Daniel Ware.[28] Although a significant member of the troupe, Sylvester remained a relatively isolated figure; not only was he one of very few African-American members, he eschewed the group's more surrealist activities for what he saw as classier, more glamorous performances onstage.[29] In the Cockettes' performances, he was usually given an entire scene to himself, often with little relevance to the narrative and theme of the rest of the performance, although through doing so, he gained his own following.[30] With a piano player named Peter Mintum, Sylvester worked on solo scenes in which he exhibited his interest in blues and jazz by imitating several of his musical idols like Billie Holiday and Josephine Baker.[7][31] Adding to his image, Sylvester began using the pseudonym Ruby Blue, and described himself as "Billie Holiday's cousin once removed."[32] Fascinated by black musical heritage, he read up on obscure and widely unknown black musicians, and considered writing a book on the subject. A collector of "negrobilia," in some of his Cockette performances, he played up to racial stereotypes of African-Americans in order to ridicule the stereotypes themselves.[33]

On New Year's Eve 1970, Sylvester met and fell for a young white audience member, Michael Lyons, who was then suffering with a heroin addiction. Sylvester immediately proposed marriage, and they entered a relationship and moved in together. Although same-sex marriage was then illegal throughout the United States, the couple held a wedding in the Shakespeare Garden of Golden Gate Park, in which they proclaimed their love for each other. In keeping with their free love values, they agreed to have other sexual partners and would give each other away to friends as birthday presents.[34] Meanwhile, the Palace Theatre's manager, Sebastian, thought highly of Sylvester and his act, and invited him to appear in a spoof film, Tricia's Wedding, which parodied the marriage of Tricia Nixon Cox, daughter of President Richard Nixon. In the film, Sylvester played the role of both Coretta Scott King and the African ambassador Miss Uma King.[35][36] In 1971, Sylvester was given his own one-man show at the Palace Theater; entitled Sylvester Sings; it involved him covering a number of songs accompanied by Mintum on piano.[37] He nevertheless remained a part of the Cockette troupe during their divisive split, in which Hibiscus and his followers left to form the Angels of Light. Following Hibiscus' departure, the Cockettes began to gain increasing media attention, with celebrities such as Rex Reed, Truman Capote, and Gloria Vanderbilt enthusing about their performances. Rolling Stone magazine singled out Sylvester's performances for particular praise, describing him as "a beautiful black androgyne who has a gospel sound with the heat and shimmer of Aretha's."[38]

The success led the troupe to decide to take their show to New York City, a city with a long history of drag culture. They traveled there in November 1971, staying at the run-down Hotel Albert on 11th Street and immediately immersing themselves in the city's avant-garde, attending parties held by Andy Warhol and Screw magazine. Spending so much of their time partying, most of the Cockettes didn't rehearse, the exception being Sylvester, who wanted to perfect his act.[39] When the opening night at the Anderson Theater came about, the Cockettes performed as they had been doing in San Francisco, but their show did not go down well with the audience or the critics, and was panned in media reviews. Sylvester's act, on the other hand, was widely praised as the highlight of the show. Realizing that he had far better prospects as a solo artist, on the second New York performance he opened his act by telling the audience, "I apologize for this travesty that I'm associated with." On the seventh performance, he opened the show by walking on, announcing that he would not perform that night because he was leaving the Cockettes, and then walked off. The Cockettes disbanded the following year.[40]

Returning to San Francisco, Sylvester was immediately offered the opportunity to record a demo album by Jann Wenner, editor of Rolling Stone magazine. Using money provided by A&M Records, the album featured a cover of Bonnie Bramlett and Leon Russell's song "Superstar," which had been a recent hit single for The Carpenters; nevertheless, A&M felt that the work wasn't commercially viable and declined to release the album.[41] For the album, Sylvester had assembled about him a group of heterosexual white males—Bobby Blood on trumpet, Chris Mostert on sax, James Q. Smith on guitar, Travis Fullerton on drums, and Kerry Hatch on bass—whom he gave the name of "The Hot Band." After A&M's initial rejection, the band provided two songs for Lights Out San Francisco, an album compiled by San Francisco's KSAN radio and released on the Blue Thumb label.[42] Gaining a number of local gigs, they were eventually asked to open for English glam rock star David Bowie at the Winterland Ballroom; the gig did not sell particularly well, and Bowie would later comment that the people of San Francisco "don't need me. They've got Sylvester," referring to their shared preference for androgyny.[43]

In early 1973, Sylvester and The Hot Band were signed by Bob Krasnow to Blue Thumb. On this label, they proceeded to produce their first album, in which they switched their sound from blues to rock, which was considered more commercially viable. The backing singers were the Pointer Sisters, who would go on to a successful musical career of their own. Sylvester would name this first album Scratch My Flower, due to a gardenia-shaped scratch-and-sniff sticker adhered to the cover, although it would instead come to be released under the title of Sylvester and his Hot Band.[7][44]Scratch My Flower consisted primarily of covers of songs by artists such as James Taylor, Ray Charles, Neil Young, and Leiber and Stoller, and would be described by Sylvester biographer Joshua Gamson as lacking in "the fire and focus of the live shows."[45] It would proceed to sell poorly.[46]

Sylvester and his Hot Band went on tour around the United States, receiving threats of violence in several Southern states, where widespread conservative and racist attitudes led to antagonism between the band and locals. Wherever possible on tour, Sylvester visited gay bathhouses where he engaged in sexual acts with other patrons.[47] In late 1973, the band recorded their second album, Bazaar, which included both cover songs and original compositions by bassist Kerry Hatch. Hatch would later comment that the Hot Band found the album more satisfactory than its predecessor, but nevertheless it once again sold poorly.[48] Finding Sylvester difficult to work with, and fed up with his lack of commercial success, the Hot Band left Sylvester in late 1974, resulting in Krasnow cancelling his recording contract.[46] At the same time, Sylvester's relationship with Michael Lyons broke down un-amicably, with the latter moving to Hawaii.[49]

Now without the Hot Band or a recording contract, Sylvester set himself up with a new band, First with Horus Jack Tolsen and then The Four A's, Amadeo Barrios (drums) Adrian Barrios (bass) Archie White (keyboards) and Angel (Fruitcake) Reyes(guitar)and a new set of backing singers, one black drag queen named Gerry Kirby and Ladee Bianca. With this new entourage, he continued to perform at a number of local venues, but reviewers were unimpressed with the new line-up since they were moving him in a funky direction, most of whom abandoned Sylvester in December 1974.[50] After a brief sojourn to England, Sylvester returned to San Francisco and assembled together three young drag queens to be his backing singers: Arnold Elzie, Leroy Davis, and Gerry Kirby. Nevertheless, although he performed at such events as the 1975 Castro Street Fair, success continued to elude him, and he eventually fired his backing singers.[51]

"Something clicked and sighed into place when Sylvester and the Tons got together – something that wasn't there with the Hot Band white boys, for all that they could cook; something that wasn't there with Peter Mintum, for all the beautiful oddness that he and Sylvester shared; something that wasn't even there with the black drag-queen singers, for all the fierceness they projected. Izora and Martha were whom he came from and who he was... They were women who got their own. They sounded right with Sylvester, and looked just right, one on either side of him. Plus, next to them, Sylvester, who had grown quite round, looked positively svelte."

Through a mutual friend he was put in contact with a woman named Brent Thomson who agreed to be his manager. Suggesting that he rid himself of the androgynous image and wear more masculine clothing in order to gain a recording contract, she also opened up auditions to find him some new backing singers. One of those auditioning was a large black woman named Martha Wash; instantly enamored with her, Sylvester asked her if she had another large black friend who could sing, after which she introduced him to Izora Rhodes. Although he referred to them simply as "the girls," Wash and Rhodes would name themselves the Two Tons O' Fun, and continued to work with Sylvester intermittently until his death, developing a close friendship with him.[53] They were soon joined by bassist John Dunstan and keyboard player Dan Reich.[54]

Playing gay bars such as The Stud and The Endup, in September 1976, Sylvester and his band gained a regular weekend job at The Palms nightclub on Polk Street, performing two or three sets a night. It was here that his show caught the attention of Nancy Pitts, wife of Motown producer Harvey Fuqua, and Fuqua subsequently signed Sylvester onto a solo deal with Fantasy Records in 1977.[55][56] In the middle of that year, he recorded his third album, the self-titled Sylvester, which featured a cover design depicting Sylvester in male attire. The songs included on the album were influenced by dance music, and included Sylvester's own compositions, such as "Never Too Late," as well as covers of such hits as Ashford & Simpson's "Over and Over." Many reviewers noted that Sylvester's image had been altered since his early career, moving him away from the glittery androgynous appearance to that of a more conventional rhythm-and-blues singer which would have wider commercial appeal. Released as a single, Sylvester's "Over and Over" proved a minor hit in the U.S., but was more successful in Mexico and Europe.[57] Building on the album's release, Sylvester proceeded on a tour of Louisiana and then Mexico City.[58]

San Francisco's Castro neighborhood, where Sylvester regularly performed and socialized among the LGBT community. Biographer Joshua Gamson described him as Castro's "undisputed First Lady".[59]

Sylvester's fame increased following the release of his solo album, and he was employed to perform regularly at The Elephant Walk gay bar in the Castro, an area of San Francisco dominated by the local gay population. He became a friend of Harvey Milk—known locally as the "Mayor of Castro Street"—who was the first openly gay man to be elected to public office in California, and performed at Milk's birthday party that year.[60] In the spring of 1978, Sylvester successfully auditioned for a cameo appearance in the film The Rose, starring gay iconBette Midler. In the film, he plays one of the drag queens singing along to Bob Seger's "Fire Down Below," in a single scene that was filmed in a run-down bar in downtown Los Angeles.[61]

Deciding to begin production on his second solo album, subsequently titled Step II (1978), Sylvester was particularly influenced by the genre of dance music known as disco which was then becoming increasingly popular across the western world. Disco was particularly associated with the gay, black, and Latino communities in the U.S., and dominated by female African-American artists such as Donna Summer, Gloria Gaynor, and Grace Jones; Sylvester would admit to initially being skeptical regarding the seriousness of disco, but recognized its increasing commercial potential. During this time, Sylvester met Patrick Cowley. Cowley had attended City College of San Francisco where he studied music, specifically the use of synthesizers. After hearing what Cowley was doing with the synthesizer, he got excited by his innovative techniques and asked him to join his studio band. The album landed Cowley a job as a back-up musician on Sylvester's subsequent world-wide tours, and the two started a close friendship and collaboration. Once again co-produced by Harvey Fuqua and released on his Fantasy label, Step II contained a number of disco songs, including "You Make Me Feel (Mighty Real)," written by James Wirrick, and "Dance (Disco Heat)," written by Eric Robinson, both of which would also be released as singles.[56][62]

Both singles proved commercial hits both domestically and abroad, topping the American dance chart and breaking into the U.S. pop charts.[63] The album itself was also a success, being certified gold, and was described by Rolling Stone magazine as being "as good as disco gets."[64] In one instance, Sylvester was rushed to London, England, at only four hours notice to give various performances and capitalize on the chart success of "Mighty Real" in Europe; he proved hugely popular in the city, being mobbed by fans and performing at a number of different nightclubs.[65] Back in the U.S., Sylvester began to appear on television shows to advertise his music, appearing on Dinah Shore, American Bandstand, Rock Concert, and The Merv Griffin Show.[66] He also undertook a series of tours across the country, opening for both The Commodores and Chaka Khan, and performing alongside The O'Jays, War, and L.T.D..[67] As a result, he earned a number of awards, and performed at several award ceremonies.[68]

Sylvester followed the success of Step II with an album entitled Stars. Consisting of four love songs, the title track had been written by Sylvester's friend and collaborator Patrick Cowley, and Sylvester would proceed to tell the press that it was his first completely disco album, but that it would also probably be his last. He premiered the album's four tracks on March 11, 1979, at a sold-out show in the San Francisco War Memorial Opera House. The performance was attended by a number of senior figures in local government, and halfway through, Mayor Dianne Feinstein sent her aide, Harry Britt, to award Sylvester with the key to the city and proclaim March 11 to be "Sylvester Day."[69] The Opera House gig was recorded, and subsequently released as a live album, Living Proof.[70]

Despite increasing mainstream success, Sylvester continued to reaffirm his connection to the gay community of San Francisco, performing at the main stage at the 1979 Gay Freedom Day parade.[71] That same year, Sylvester met the singer Jeanie Tracy through Harvey Fuqua, and they immediately became friends. A large black woman, Sylvester felt that Tracy would work well with his Two Tons O' Fun, and invited her to join his backing singers, which she would proceed to do. Subsequently befriending the Tons, she would work for Sylvester for the rest of his life.[72] The Tons themselves were convinced by Fuqua to produce their own self-titled album, from which came two dance chart hits, "Earth Can Be Just Like Heaven" and "Just Us"; as a result, they began to work less and less with Sylvester, only joining him on occasion for his live shows.[73]

In 1980, Sylvester produced his next album for Fantasy Records, Sell My Soul. Avoiding disco after the latter had become unpopular following the much publicized Disco Sucks movement, Sell My Soul instead represented a selection of soul-inspired dance tracks. Recorded in two weeks, Sylvester worked largely with backing singers and musicians whom he was unfamiliar with, and regular collaborators Izora Rhodes and Patrick Cowley were entirely absent. Reviews were generally poor, describing the album as being average in quality.[74] That year, Sylvester also reached tabloid headlines after he was arrested on a visit to New York City, accused of being involved in the robbery of several rare coins; it was later revealed to have been a set-up, and Sylvester was never charged.[9][75]

Sylvester's fifth and final album for Fantasy Records was Too Hot to Sleep, in which he once again eschewed disco for a series of groove soul tunes, ballads, and gospel-style tracks. Missing the Two Tons entirely, Jeanie Tracy was instead accompanied by a new backing singer, Maurice "Mo" Long, and because the three of them had all grown up in the Church of God in Christ, they decided to refer to themselves as the "C.O.G.I.C. Singers." The album also featured a number of tracks in which Sylvester avoided his usual falsetto tones to sing in a baritone voice.[76]

In 1982, Sylvester, like the Two Tons, came to believe that Harvey Fuqua and Fantasy Records had failed to pay him everything that he was owed from the success of his records. His relationship with Fuqua broke down, and he decided to leave the label. In November 1982, he filed a lawsuit against them, which ultimately proved successful in establishing that the company had been withholding money from him totaling $218,112.50. Nevertheless, Fuqua proved unable to pay anything more than $20,000, meaning that Sylvester never saw the majority of the money that was legally owed to him. Sylvester grew to despise Fuqua, and forbade his friends from ever mentioning his name.[77] Hiring an old friend named Tim McKenna as manager, Sylvester then decided to record his next album with Megatone Records, a club-orientated company that had been founded by Patrick Cowley and Marty Blecman the previous year and whose customers were primarily gay clubbers from San Francisco.

Sylvester was still a well-known fixture of the San Francisco gay scene when doctors announced the discovery of a fatal disease that was spreading through the community. Initially designated as Gay-related immune deficiency (GRID), it would later be renamed HIV/AIDS after it was discovered that the majority of those infected worldwide were heterosexual. Patrick Cowley (1950–1982), was diagnosed with the disease, and despite his deteriorating physical condition, continued to work on new tracks for his own solo albums and for Sylvester.

The first Sylvester album on Megatone was All I Need, released in 1982, for which James Wirrick had written and produced most of the songs, which were dance-orientated and influenced by the new wave music then in vogue. Sylvester himself insisted that he get to include several ballads on the album. The best known song on the album, however, was the Patrick Cowley penned and produced "Do Ya Wanna Funk," a Hi-NRG dance track which would be released as a single on 4 July 1982, heading to the top of the dance charts and entering the pop charts in a number of countries across the world.[78] The album included cover art depicting Sylvester as an Egyptian princess created by Mark Amerika.[79] The album would be renamed "Do Ya Wanna Funk" when it was reissued in 2003 by Canadian label Unidisc.

While on tour in London later that year, preparing to perform at the Heaven club, Sylvester learned of Cowley's death on 12 November 1982. He proceeded to go onstage, where he informed the crowd of Cowley's passing and then sung "Do Ya Wanna Funk" in memory of him.[80]

His second album for Megatone was entitled Call Me (1983), but it did not prove to be a commercial success. Only one single from the album, "Trouble in Paradise," did manage to enter the top 20 of the U.S. dance charts, and Sylvester would later relate that that particular song was his "AIDS message to San Francisco."[81] Sylvester was emotionally moved by the HIV/AIDS epidemic, and began helping out at the Rita Rockett Lounge for patients of the disease at the San Francisco General Hospital as well as performing at various benefit concerts to raise money and awareness to combat the spread of the disease.[82] In February 1984, he also performed a "One Night Only" retrospective of his work at the prestigious Castro Theatre, but unlike in his heyday, this time, tickets failed to sell out. As he proceeded to tour around the country, he found that demand for his performances was going down, and he was playing to smaller venues, and singing to a pre-recorded tape rather than to a live band.[83]

His next album, entitled M-1015 (1984), was more frenetic and pumping than his previous releases, having completely embraced the genre of Hi-NRG. The major figures behind the album had been Kessie and Morey Goldstein, and Sylvester himself had not written any of the tracks.[84] That year, he also entered into a relationship with an architect named Rick Cramner, and together they moved into a new apartment in the hills, where Sylvester decorated his powder room with posters and memorabilia of Divine (1945–1988), the drag queen, actor, and singer whom he had briefly known when they were in The Cockettes.[85] Also in 1984, Sylvester added lead vocals to the 1981 Patrick Cowley hit "Menergy" and released it as a single.

Sylvester's final album, Mutual Attraction (1986), was produced by Megatone but licensed and released by Warner Bros. Records. On the album, Sylvester had worked with a wide number of collaborators, and included new tracks alongside covers of songs by Stevie Wonder and George Gershwin. Reviews of the album were mixed, with many claiming that it was a poor release. One of the album's singles, "Someone Like You," proved more successful, reaching number one on the Billboard dance charts.[86] Warner Bros. booked him to appear on the New Year's Eve edition of The Late Show Starring Joan Rivers, during which Joan Rivers described him as a drag queen; visibly annoyed, he corrected her by stating that he was not a drag queen, proclaiming simply "I'm Sylvester!"[56][87]

Sylvester's partner, Rick Cranmer, became aware that he had become infected with HIV in 1985. With no known medical cure, his health deteriorated rapidly, and he died in September 1987, leaving Sylvester devastated.[9] Although he recognized that he too was probably infected, Sylvester refused to have his blood tested, only noticing the virus' first symptoms when he developed a persistent cough.[88] Beginning work on an album that would remain unfinished, he moved into a new apartment on Collingwood Street in the Castro, and tried his best to continue performing, even though he became too sick to undertake a full tour. Hospitalized for sinus surgery in late 1987, upon returning to his apartment, he began to be cared for by his mother and an acquaintance Jean Tracy, while other family to visit him; he would proceed to give away many of his treasured items and would write up his will. He refused to take zidovudine, an antiretroviral drug that had serious side effects. Having lost a lot of weight and unable to walk very far, he was pushed along in a wheelchair at the 1988 Gay Freedom Parade in the Castro, just in front of the People with AIDS contingent; along Market Street, assembled crowds shouted out his name as he passed.[9] The subsequent 1988 Castro Street Fair was named "A Tribute to Sylvester," and although he was too ill to attend, crowds chanted his name to such an extent that he was able to hear them from his bedroom.[89][90] He continued to give interviews and took part in AIDS activism, in particular highlighting the devastation that it was wreaking in the African-American community. In an interview with the NME, he stated, "I don't believe that AIDS is the wrath of God. People have a tendency to blame everything on God."[91]

For Thanksgiving 1988, his family came over to spend the holiday with him, by which time he was becoming increasingly bed-ridden and reliant on morphine to ease his pain. He proceeded to die in his bed on December 16, 1988 at the age of 41.[92] Sylvester had already planned his own funeral, insisting that he be dressed in a red kimono and placed in an open-top coffin for the mourners to see, with his friend Yvette Flunder doing his corpse's makeup.[9] He wanted Jean Tracy to sing at his funeral, accompanied by choirs and many flowers. The whole affair took place in his church, the Love Center, with a sermon being provided by Reverend Walter Hawkins. The event was packed, with standing room only, and the coffin was subsequently taken and buried at his family's plot in Inglewood Park Cemetery.[93]

"Perhaps Sylvester suffered the curse of the control queen and the narcissist: he chose controllable and adoring partners, only to find out that they were not self-possessed enough to meet him where he wanted to be met. But his was also the curse of the generous and gentle-hearted. He used the nurturing talents that Letha and JuJu gave him, teaching people... that they, too, were loved and fabulous. When he succeeded, they were ready to go out on their own. You ask one person and he'll say that Sylvester just wanted a worshipful housewife; ask another and he'll tell you that Sylvester wanted to give his soul away to someone extraordinary enough to handle it. They are both right, no doubt."

Sylvester was openly gay, with biographer Joshua Gamson noting that he tended to enter into relationships with men who were "white, self-doubting and effeminate."[95] In 1978, he met a model named John Maley at a San Francisco show, and the slim, white Catholic boy soon moved in to live with Sylvester at his apartment. Sylvester later devoted the song "Can't Forget the Love" from his Too Hot to Sleep album to his young lover, but their relationship broke up when Maley decided to move to Los Angeles; he would later recollect that Sylvester "was a lovely man, and I owe him a lot."[96] In 1981, Sylvester entered into a relationship with a skinny brunette from Deep River, Connecticut named Michael Rayner, but unlike his predecessors, he did not move into Sylvester's house; their partnership ended as soon as Rayner admitted that he hadn't fallen completely in love with Sylvester.[97] Sylvester's next major relationship was with Tom Daniels, a hairdresser whom he met in 1982, but their romance ended after six months when Daniels discovered that Sylvester had been having sex with other men while on tour.[98] His final partner, Rick Cranmer, was a six foot two blonde with blue eyes, whom he had first met at one of his gigs in 1984. An architect, he and Sylvester would eventually move into a house together in the hills. Cranmer would die of AIDS in 1987, the year before Sylvester also succumbed to the virus.[85]

Sylvester was considered to be a prima donna by members of the Hot Band and could be temperamental and difficult with those whom he worked with.[9][45] He found it difficult saving the money that he earned, instead spending it as soon as he obtained it, both on himself and on his lovers, friends, and family.[99] As an openly gay man throughout his career, Sylvester came to be seen as a spokesman for the gay community. He recognized this, but remarked that he felt his career had "transcended the gay movement. I mean, my sexuality has nothing to do with my music. When I'm fucking I'm not thinking about singing and vice versa." He was particularly critical of "clones" – gay men who dressed alike with boots, boot-cut jeans, checked shirts and handlebar mustaches—stating that all too often they judged those gay people who were flamboyant or extravagant.[100]

Sylvester was very self-conscious about his physical appearance, and when he obtained enough money from the successful Step II album (1978), he spent part of it on cosmetic surgery to remove a bump on his nose, inject silicone into his cheeks, and have cosmetic work done on his teeth.[101] He would also insist that all pictures of himself were meticulously airbrushed.[102]

Sylvester was born and raised into the Pentecostal denomination of Christianity, and remained a Christian throughout his life. He would often compare the ecstatic feelings that accompanied his onstage performances with the feelings experienced in a gospel choir in a Pentecostal church. When performances reached a certain level of heightened emotion, he would comment that "we had service."[103] In later life, he joined the Love Center Church in East Oakland, a ministry founded by the preacher and former gospel singer Walter Hawkins in the 1970s. He had been introduced to the church by Jean Tracie in the 1980s, and he would soon become a regular churchgoer, enjoying the place's welcoming attitude towards societal outcasts. Sylvester would request that his funeral be undertaken by the ministry at the Love Center.[104]

During the late 1970s, Sylvester gained the moniker of the "Queen of Disco."[105] This term would continue to be given to the singer into the 21st century.[106] The English journalist Stephen Brogan later described him as "a star who shined brightly. He only happened once. He was a radical and a visionary in terms of queerness, music and race."[107]

A biography of Sylvester was authored by the sociologist Joshua Gamson and published in 2005.[108] Writing for the London-based LGBT magazine Beige: The Provocative Cultural Quarterly, Stephen Brogan expressed his opinion that while Gamson's biography was well researched, it had a fragmented structure and as such was "not a joy to read".[107]Entertainment Weekly called the book "playful and furious",[109]The Boston Globe suggested that it was "as engaging as the times it so energetically resurrects",[110] and The San Francisco Chronicle reported that the author "carefully paints the shifting social tapestry into his subject's life story without ever taking Sylvester out of the foreground".[111]The Fabulous Sylvester won the 2006 Stonewall Book Award for nonfiction.[112]

In 2011, the TV series Unsung aired an episode on Sylvester, that was later made available through YouTube.[107]Sylvester: Mighty Real, the official feature-length documentary on the life and career of Sylvester, is currently in production. The film features interviews with members of Sylvester's family and other artists and musicians who have been inspired by, and worked with Sylvester through the years, but by 2012, Brogan noted that the film's progress had halted.[107]

In August 2014, an Off-Broadway musical titled Mighty Real: A Fabulous Sylvester Musical, is scheduled to begin in New York City.[113]